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I think that was the moment when he realized she was much more than just a chick who liked playing bad-girl.
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I think he always knew, actually. He just didn't count on it being necessary to find out what that "much more" entailed. Dylan tried to nip that possibility in the bud early on when he told her he didn't want anything to do with her if she lived at the Walsh house. "You're
Valerie?" So much for his anonymous one-night-stands with no accountability.
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She moved him because he recognized someone who was struggling as well, imo.
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That mirroring was part of the attraction. Both disenchanted with the "phony", judgmental people around them, both with dead fathers, both trying to escape from themselves (Dylan more so -- I think Valerie had a different stake, more to do with controlling how people react to her).
Apart from moving him, Dylan was also in a unique position of vulnerability with her early on. This woman who's supposed to be emotionally disposable is the only one who knows the secret he's carrying, that he lost all his money in a scheme and for some reason needs to pretend, for his friends, that it didn't happen. She already knows that he fears being disowned by those who supposedly don't matter anymore.